CN114989120A - Benzofuran luminescent liquid crystal compound and synthesis method and application thereof - Google Patents
Benzofuran luminescent liquid crystal compound and synthesis method and application thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 82
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 73
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000001308 synthesis method Methods 0.000 title abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 238000002156 mixing Methods 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 15
- 229940125904 compound 1 Drugs 0.000 claims description 14
- 229940125782 compound 2 Drugs 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
- 229940126214 compound 3 Drugs 0.000 claims description 11
- 239000011259 mixed solution Substances 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 9
- 230000002194 synthesizing effect Effects 0.000 claims description 9
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 claims description 8
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 claims description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 claims description 5
- 238000010791 quenching Methods 0.000 claims description 5
- 230000000171 quenching effect Effects 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 claims description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 238000003760 magnetic stirring Methods 0.000 claims description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
- 229960002317 succinimide Drugs 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VXJTWTJULLKDPY-UHFFFAOYSA-N 1-bromo-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(Br)C=C1 VXJTWTJULLKDPY-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13731—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on a field-induced phase transition
- G02F1/13737—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on a field-induced phase transition in liquid crystals doped with a pleochroic dye
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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Abstract
A benzofuran luminescent liquid crystal compound, a synthesis method and an application thereof are disclosed, wherein the benzofuran luminescent liquid crystal compound is characterized in that the general formula of the chemical structural formula of the benzofuran luminescent liquid crystal compound is as follows:
wherein n represents the number of alkyl chains and has a value range of 3-5. The invention enhances dichroism, improves optical anisotropy and dielectric anisotropy, widens wide liquid crystal phase interval, has good chemical stability and thermal stability, and has good response in display devices under the condition that the rotational viscosity is hardly influencedHas good application especially in host-guest display devices.
Description
Technical Field
The invention relates to the technical field of luminescent liquid crystal materials, in particular to a benzofuran luminescent liquid crystal compound and a synthesis method and application thereof.
Background
With the gradual development of liquid crystal displays, the application of the traditional thin film transistor liquid crystal display (TFT-LCD) is wide, but the defects of complex process, large energy consumption and the like are paid attention to by people all the time. The TFT-LCD mainly comprises components such as a backlight source, a polarizing film, a liquid crystal layer, a thin film transistor, a color filter and the like, the backlight source has great loss of light transmittance after passing through each component, wherein the polarizing film and the filter layer consume the most energy, and the light transmittance finally presented to eyes of people is only 5 percent, so that the energy consumption loss is great and the attention of people is attracted. The traditional liquid crystal does not emit light and can display under the modulation of an external light source, and in the whole display process, the liquid crystal plays a role of a voltage-controlled light valve and belongs to a passive type.
In recent years, dichroic displays are favored, and the principle of the dichroic displays is that guest dye molecules and parent liquid crystal molecules are mixed to obtain a luminescent material, the molecules are orderly arranged under the condition of a switching electric field to show a difference between light and shade, and a liquid crystal layer actively emits light.
The use of luminescent liquid crystal materials to replace guest dye molecules is a necessary trend, and the following advantages and disadvantages exist: although the mixed crystal formula prepared by guest dye molecules can provide strong fluorescence emission intensity, most of the dye molecules are colored, and the solubility is generally poor, so that the mixed crystal viscosity is increased, and even the liquid crystal phase behavior is lost. If the dye molecules are converted into the luminescent liquid crystal molecules, many problems which cannot be solved by the dye molecules can be solved, for example, the self color can be colorless, and the comprehensive performance (birefringence and dielectric anisotropy) of the liquid crystal is expected to be improved.
In the existing literature on designing and synthesizing luminescent liquid crystal molecules, the structural design is complex, the solubility is general, the rotational viscosity is not characterized, and the specific influence of the introduction of the luminescent liquid crystal molecules on the birefringence and the dielectric anisotropy is not considered, so that the liquid crystal performance is poor when the luminescent liquid crystal molecules are applied to a host-guest display.
The prior literature on luminescent liquid crystal molecules is:
[1]Lu H,Xu C,Li Z,et al.High-contrast electrically switchable light-emitting liquid crystal displays based onα-cyanostilbenic derivative[J].Liquid Crystals,2018,45(1):32-39.
[2]Zhang D,Liu Y,Gao H,et al.α-Cyanostilbene and fluorene based bolaamphiphiles:synthesis,self-assembly,and AIEE properties with potential as white-light emissive materials and light-emitting liquid crystal displays[J].Journal of Materials Chemistry C,2020,8(48):17474-17481.
[3]Zhao D,Bi W,Tang B Z.A Light-Emitting Liquid Crystal Display Device without Polarizers and Alignment Layers[J].Advanced Optical Materials,2021,9(19):2100489.
[4]Tan X,Chang Q,Su F,et al.Rodlike 4,6-diamino-1,3,5-triazine derivatives,effect of the core length on mesophase behavior and their application as LE-LCD device[J].Journal of Molecular Liquids,2022,346:117879.
disclosure of Invention
In order to solve the technical problems in the prior art, the invention provides a benzofuran luminescent liquid crystal compound, a synthesis method and an application thereof.
In order to achieve the purpose, the invention provides a benzofuran luminescent liquid crystal compound, a synthesis method and an application thereof, wherein the general formula of the chemical structural formula of the benzofuran luminescent liquid crystal compound is as follows:
wherein n represents the number of alkyl chains and has a value range of 3-5.
As another aspect of the present invention, the present invention further provides a method for synthesizing a benzofuran luminescent liquid crystal compound, comprising the following steps:
s1, taking a compound 1 with a structural formula shown as a general formula (1) and a compound 2 with a general formula (2);
wherein the value range of n is 3-5;
mixing the compound 1 with triethylamine, then adding cuprous iodide and triphenylphosphine, heating to 65 ℃, stirring for 30min, adding bis (triphenylphosphine) palladium dichloride and a mixed solution of the compound 2 and the triethylamine, and reacting for 12h to obtain a crude product; adding potassium carbonate, methanol and N, N-dimethylformamide into the crude product, heating to 50 ℃, and reacting for 8 hours to obtain a compound 3 with a structural formula shown as the following general formula (3):
wherein the value range of n is 3-5;
s2, mixing the compound 3 with tetrahydrofuran, cooling to-78 ℃, slowly adding lithium diisopropylamide dropwise, reacting for 3 hours, adding saturated ammonium chloride solution for quenching, and obtaining a compound 4 with the structural formula (4) as shown in the following formula, namely the benzofuran luminescent liquid crystal compound:
wherein the value range of n is 3-5.
As a further preferred embodiment of the present invention, compound 1 in step S1 is synthesized by the following method:
s1.1, mixing 2,2, 2-trifluoroethanol, triethylamine and dichloromethane, placing at the temperature of 0-20 ℃, adding a mixed solution of methanesulfonyl chloride and dichloromethane, reacting for 12-24h, adding a hydrochloric acid solution for quenching, and reacting for 1h under magnetic stirring to obtain a compound 1-1 of the following general formula (1-1):
s1.2, mixing the compound 1-1, catechol, potassium carbonate and N, N-dimethylformamide, heating to 80-100 ℃, adding potassium iodide after 30min, and reacting for 12-24h to obtain a compound 1-2 with a structural formula shown in the following general formula (1-2):
s1.3, mixing anhydrous aluminum chloride and dichloromethane, stirring for 10-30min at-30 ℃, adding a mixed solution of acetyl chloride and dichloromethane and a mixed solution of a compound 1-2 and dichloromethane, and reacting for 4-8h to obtain a compound 1-3 of the following general formula (1-3):
s1.4, mixing the compound 1-3, m-chloroperoxybenzoic acid, trifluoroacetic acid and dichloromethane, placing the mixture in an ice water bath, cooling to 0-10 ℃, stirring for 10-30min, and then placing the mixture in room temperature for reacting for 24-48h to obtain a compound 1-4 of the following general formula (1-4):
s1.5, mixing the compounds 1-4, N-succinimide and trifluoroacetic acid, heating to 50-80 ℃, and reacting for 12-24h to obtain the compound 1 with the following structural formula (1):
as a further preferred embodiment of the present invention, compound 2 in step S1 is synthesized by the following method:
s1.6, taking a compound 2-1 with a structural formula shown as the following general formula (2-1);
wherein the value range of n is 3-5;
mixing the compound 2-1, p-bromoiodobenzene, anhydrous potassium carbonate, tetrabutylammonium bromide, water, tetrakis (triphenylphosphine) palladium and N, N-dimethylformamide, stirring at 80-100 ℃, and reacting for 8-12h to obtain a compound 2-2 of the following general formula (2-2):
wherein the value range of n is 3-5;
s1.7, mixing a compound 2-2, 2-methyl-3-butyn-2-ol and triethylamine, stirring at 60-80 ℃ for 10-30min, and adding cuprous iodide, triphenylphosphine and tetrakis (triphenylphosphine) palladium to obtain a crude product; adding alkynol, sodium hydroxide, ethylene glycol ethyl ether and toluene into the crude product, heating to 60-80 ℃, and reacting for 6-10h to obtain a compound 2 with the structural formula as shown in the following general formula (2):
wherein the value range of n is 3-5.
In a further preferred embodiment of the present invention, in step S2, lithium diisopropylamide and a saturated ammonium chloride solution are both added dropwise through a constant pressure dropping funnel.
In a further preferred embodiment of the present invention, in step S1, the molar ratio of compound 1 to compound 2 is 1: 0.5-1.5.
As a further preferred embodiment of the present invention, in step S2, the amount of tetrahydrofuran used per gram of compound 3 is 50-100 mL.
As another aspect of the invention, the invention also provides application of the benzofuran luminescent liquid crystal compound in a liquid crystal display.
As a further preferable technical solution of the present invention, the liquid crystal display is a host-guest mode liquid crystal display.
The benzofuran luminescent liquid crystal compound and the synthesis method and the application thereof can achieve the following beneficial effects by adopting the technical scheme:
1) the synthesis method of the benzofuran luminescent liquid crystal compound has the advantages of mild reaction, no pollution, simple and convenient operation, low cost, lower requirements on equipment and process conditions, easy realization of industrial production under the existing conditions, provision of a new technical solution way and a new idea for improving the liquid crystal performance of mixed crystals, and high synthesis yield and purity;
2) the benzofuran luminescent liquid crystal compound disclosed by the invention is applied to a mixed crystal formula to prepare a novel mixed crystal, so that the dichroism of the compound is enhanced, the optical anisotropy and the dielectric anisotropy are improved, a wide liquid crystal phase interval is widened under the condition that the rotational viscosity is hardly influenced, and the compound has good chemical stability and thermal stability, has good application in a display device, and particularly has good application in a host-guest display device.
Drawings
The present invention will be described in further detail with reference to the accompanying drawings and specific embodiments.
FIG. 1 is a graph showing the results of testing compound 5PP-OCF2 for fluorescence emission intensity and dichroism;
FIG. 2 is a graph showing the test results of Compound 5PP-OCF2 in the clearing point test;
FIG. 3 is a hydrogen spectrum of Compound 3PP-OCF 2;
FIG. 4 is a carbon spectrum of Compound 3PP-OCF 2;
FIG. 5 is an infrared characterization of Compound 3PP-OCF 2.
The objects, features and advantages of the present invention will be further explained with reference to the accompanying drawings.
Detailed Description
The invention will be further described with reference to the accompanying drawings and specific embodiments. In the preferred embodiments, the terms "upper", "lower", "left", "right", "middle" and "a" are used for clarity of description only, and are not used to limit the scope of the invention, and the relative relationship between the terms and the terms is not changed or modified substantially without changing the technical content of the invention.
The invention provides a benzofuran luminescent liquid crystal compound, which has a chemical structural formula as follows:
wherein n represents the number of alkyl chains and has a value range of 3-5.
The benzofuran luminescent liquid crystal compound provided by the invention can be applied to liquid crystal displays, particularly host-guest mode liquid crystal displays, and can show excellent liquid crystal performance. The benzofuran luminescent liquid crystal compound has good solubility and good conjugation, has high fluorescence emission intensity and obvious dichroism, and improves the birefringence and dielectric anisotropy, thereby widening the liquid crystal phase interval.
In order to further understand the technical scheme of the present invention, the following embodiments are further detailed to describe the technical scheme of the present invention for synthesizing benzofuran luminescent liquid crystal compounds.
Example 1
A synthetic method of benzofuran luminescent liquid crystal compounds comprises the following steps:
1) synthesis of Compound 1-1:
adding 20g of 2,2, 2-trifluoroethanol, 30.6mL of triethylamine and 200mL of dichloromethane into a 1000mL single-mouth bottle in sequence, and placing at-10 ℃; dropwise adding a mixed solution of 17mL of methanesulfonyl chloride and 100mL of dichloromethane into a single-mouth bottle, and reacting for 12h in total; slowly dripping 100mL of hydrochloric acid (1M) solution into the system for quenching, and reacting for 1h under magnetic stirring; the post-treatment gave 35g of Compound 1-1 in a GC purity of 99% in a yield of 90%, the compound 1-1 having the following formula (1-1):
2) synthesis of Compounds 1-2:
adding 10.00g of catechol, 36g of compound 1-1, 38g of potassium carbonate and 200mL of N, N-dimethylformamide into a 500mL three-neck flask in sequence, heating to 80 ℃, adding 0.31g of potassium iodide after 30min, and reacting for 12 h; the post-treatment gave 12.15g of the compound 1-2 with a GC purity of 99% in a yield of 72%, the compound 1-2 having the following formula (1-2):
3) synthesis of Compounds 1-3:
adding 7.43g of anhydrous aluminum chloride and 100mL of dry dichloromethane into a 500mL single-neck flask in sequence, stirring for 10min in a low-temperature reaction bath at minus 30 ℃, adding 5.2mL of acetyl chloride and 60mL of dichloromethane mixed solution, finishing dropping for 30min, adding 10g of L mixed solution of compound 1-2 and dichloromethane 50m into a constant-pressure dropping funnel, finishing dropping for 30min, and reacting for 4 h; the post-treatment gave 9.85g of the compound 1-3 with a GC purity of 99% and a yield of 85%, the compound 1-3 having the following formula (1-3):
4) synthesis of Compounds 1-4:
adding 5.00g of compound 1-3, 5.46g of m-chloroperoxybenzoic acid, 2.7g of trifluoroacetic acid and 30mL of dichloromethane into a 100mL Schlenk tube in turn, placing the mixture into an ice water bath, cooling to 0 ℃, stirring for 30min, and then placing a reaction system at room temperature for reaction for 48 h; the post-treatment gave 4.45g of the compound 1-4 with a GC purity of 99% and a yield of 85%, the compound 1-4 having the following formula (1-4):
5) synthesis of Compound 1
Adding 5g of compound 1-4, 3.73g N-succinimide and 0.52g of trifluoroacetic acid into a 250mL single-neck flask in sequence, heating to 80 ℃, and reacting for 12 h; the work-up gave 3g of compound 1 with a GC purity of 99% in a yield of 43%, the compound 1 having the formula (1):
6) synthesis of Compound 2-2
Taking a compound 2-1 with a structural formula shown as a general formula (2-1);
wherein, the value range of n is 3-5, in the example, n is 5;
adding 10.00g of p-bromoiodobenzene, 6.50g of compound 2-1, 7.80g of anhydrous potassium carbonate, 6.00g of tetrabutylammonium bromide, 20mL of water, 0.79g of tetrakis (triphenylphosphine) palladium and 100mL of N, N-dimethylformamide into a 250mL three-necked flask, stirring and heating, controlling the temperature to be 80 ℃, and reacting for 8 hours; the post-treatment gave 9.80g of compound 2-2 with a purity of 99% GC and a yield of 89%, which compound 2-2 had the following formula (2-2):
wherein the value of n is 5.
7) Synthesis of Compound 2
6.00g of compound 2-2 (4-bromo-4 '-pentyl-1, 1' -biphenyl), 2.36g of 2-methyl-3-butyn-2-ol and 150mL of dried triethylamine are added into a 250mL three-necked bottle, stirring is started, the temperature is raised to 65 ℃, stirring is carried out for 30min, then 0.03g of cuprous iodide, 0.03g of triphenylphosphine and 0.47g of tetrakis (triphenylphosphine) palladium are sequentially added, and a crude product is obtained after post-treatment. 4.95g of alkynol, 4.06g of sodium hydroxide, 40mL of ethylene glycol ethyl ether and 120mL of toluene of the product are sequentially added into a 250mL three-necked flask, the temperature is raised to 80 ℃, and the reaction is carried out for 6 hours. The post-treatment gave 3.07g of compound 2 having a purity GC of 98% and a yield of 70.3%, the structural formula of compound 2 being represented by the following general formula (2):
wherein the value of n is 5.
8) Synthesis of Compound 3
Adding 2.00g of compound 1 and 100mL of dry triethylamine into a 250mL three-neck flask, then adding 0.02g of cuprous iodide and 0.06g of triphenylphosphine, heating to 65 ℃, and stirring for 30 min; then adding 0.16g of bis (triphenylphosphine) palladium dichloride, dissolving 1.2g of the compound 2 in 20mL of dry triethylamine solution, slowly dropwise adding the solution, reacting for 12 hours, stopping the reaction, and performing post-treatment to obtain a crude product; carrying out the next reaction on the crude product according to the theoretical equivalent, sequentially adding 6g of potassium carbonate, 50mL of methanol and 50mL of N, N-dimethylformamide into a 250mL single-mouth bottle, heating to 50 ℃, and reacting for 8 hours; the work-up gave 1.0g of compound 3 with a GC purity of 98% in 43% yield, the compound 3 having the formula shown below in formula (3):
wherein the value of n is 5.
9) Synthesis of Compound 4
Adding 0.5g of compound 3 and 30mL of dry tetrahydrofuran into a 100mL three-neck flask, cooling to-78 ℃, measuring 10mL of lithium diisopropylamide, placing the lithium diisopropylamide into a constant-pressure dropping funnel, slowly dropping the lithium diisopropylamide, reacting for 3h, and adding 30mL of saturated chlorineQuenching the ammonium chloride solution in a constant-pressure dropping funnel; with anhydrous Na 2 SO4 dried, spin dried, petroleum ether: performing column chromatography by using ethyl acetate 50:1 as an eluent to obtain a crude product, and then performing recrystallization by using methanol to obtain a final product, namely a compound 4 which is a benzofuran luminescent liquid crystal compound and has a white solid content of 0.3g, wherein the GC purity is 98% and the yield is 45%, and the structural formula of the compound 4 is shown as the following general formula (4):
wherein, the value of n is 5, and the compound 4 is abbreviated as 5PP-OCF 2.
As can be seen from example 1, the synthetic route of the invention has good yield, and reactions such as etherification, acylation, B-V oxidation, iodination, Sonogashira coupling, ring closure under alkali conditions, LDA HF removal and the like are involved in the synthetic process. It should be noted that the post-treatment involved in the synthetic route of the present invention is a conventional operation means in the chemical field, which includes but is not limited to one or more of washing, filtering, drying, and column chromatography, and can be reasonably selected according to the needs in practical application.
The final product obtained in example 1 (hereinafter, referred to as 5PP-OCF2) was incorporated into 5536 mother liquid crystal (Δ n ═ 0.0995, Δ ∈ ═ 5.453, and the main components were 3HHV and alkylcyclohexane compounds), and the following performance tests were performed on 5PP-OCF2 doped with different mass fractions in the 5536 mother liquid crystal, respectively, and the test items are shown in table 1.
TABLE 1 specific items of Performance test
1. Fluorescence emission intensity test: as shown in fig. 1, the fluorescence emission intensity of 5PP-OCF2 in the liquid crystal cell (thickness of 5 μm) in parallel (PL//) and perpendicular (PL ″) orientations at a certain mass fraction showed an increasing trend, the material showed obvious dichroism, and the fluorescence emission intensity was increased with the increase of the concentration of 5PP-OCF2, wherein 5PP-OCF2 showed the strongest fluorescence emission intensity at wt% ~ 2.0% in 5536 matrix liquid crystal.
2. Fluorescence quantum yield test: the test results are shown in table 2.
2. Fluorescence quantum yield test results
In table 2, 5536(/ /) indicates the fluorescence quantum yield of the 5536 mother liquid crystal doped with 5PP-OCF2, and analysis of table 2 shows that the fluorescence quantum yield is highest at 3% by weight.
3. Optical anisotropy test: the test results are shown in table 3.
3. Results of optical anisotropy test
Analysis table 3 shows that the optical anisotropy tends to increase with the increase of the guest molecule, indicating that the compound itself has a positive optical anisotropy.
4. Dielectric anisotropy test: the test results are shown in table 3.
4. Dielectric anisotropy test results
Analysis of table 4 shows that the dielectric anisotropy increases with the increase of the guest molecule, indicating that the compound itself has a positive dielectric anisotropy.
5. Clearing point test: the test results are shown in fig. 2. As can be seen from the analysis of FIG. 2, as the number of guest molecules increases, the clearing point is increased by about 1 ℃ compared to that of the pure 5536 mother liquid crystal at a guest molecule content of 3%.
6. And (3) viscosity testing: the test results are shown in Table 5.
5. Results of viscosity measurement
Analysis of table 5 shows that with the increase of guest molecules, the viscosity of 5536 mixed crystal formulation is hardly affected due to good mutual solubility.
In conclusion, the mixed crystal formula provided by the invention has the advantages of stronger fluorescence emission intensity, good dichroism, improved optical anisotropy and dielectric anisotropy, widened liquid crystal phase interval and smaller viscosity influence. The compound is prepared into a mixed crystal formula to be applied to a liquid crystal display, particularly a display device in a host-guest mode, and the excellent liquid crystal performance of the compound can obviously improve the display effect.
For further research, in the synthesis method of the invention, when the value of the alkyl chain number n in the compound 2-1 is 3, the structural formula of the compound 3 is as follows:
(abbreviated as 3PP-OCF 3);
the compound 3(3PP-OCF3) was synthesized in the same manner as in example 1 to give the final product, Compound 4, having the following structural formula:
The hydrogen spectrum, carbon spectrum and infrared characterization chart of the compound 4(3PP-OCF2) are respectively shown in FIGS. 3, 4 and 5, and the structure of the compound is confirmed to be correct and the compound has repeatable operability.
The number of the alkyl chains of the benzofuran luminescent liquid crystal compound is 3-5, and the comprehensive comparison of the liquid crystal performance and the luminescence performance of the benzofuran luminescent liquid crystal compound with different alkyl chains is carried out, wherein 5PP-OCF2 is optimal, namely the melting point of 5PP-OCF2 is the lowest on the premise of ensuring the fluorescence emission intensity.
Although specific embodiments of the present invention have been described above, it will be appreciated by those skilled in the art that these are merely examples and that many variations or modifications may be made to the embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims.
Claims (9)
1. A benzofuran luminescent liquid crystal compound is characterized in that the chemical structural formula of the benzofuran luminescent liquid crystal compound is as follows:
wherein n represents the number of alkyl chains and has a value range of 3-5.
2. A method for synthesizing a benzofuran luminescent liquid crystal compound according to claim 1, comprising the following steps of:
s1, taking a compound 1 with a structural formula shown as a general formula (1) and a compound 2 with a general formula (2);
wherein the value range of n is 3-5;
mixing the compound 1 with triethylamine, then adding cuprous iodide and triphenylphosphine, heating to 50-80 ℃, stirring for 20-30min, adding bis (triphenylphosphine) palladium dichloride and a mixed solution of the compound 2 and the triethylamine, and reacting for 10-18h to obtain a crude product; adding potassium carbonate, methanol and N, N-dimethylformamide into the crude product, heating to 50-80 ℃, and reacting for 5-10h to obtain a compound 3 with a structural formula shown as the following general formula (3):
wherein the value range of n is 3-5;
s2, mixing the compound 3 with tetrahydrofuran, cooling to-50-80 ℃, slowly dripping lithium diisopropylamide, reacting for 2-5h, adding saturated ammonium chloride solution, and quenching to obtain a compound 4 with a structural formula shown as the following general formula (4), namely the benzofuran luminescent liquid crystal compound:
wherein the value range of n is 3-5.
3. The method for synthesizing a benzofuran-based luminescent liquid crystal compound according to claim 2, wherein the compound 1 in the step S1 is synthesized by:
s1.1, mixing 2,2, 2-trifluoroethanol, triethylamine and dichloromethane, placing at the temperature of 0-20 ℃, adding a mixed solution of methanesulfonyl chloride and dichloromethane, reacting for 12-24h, adding a hydrochloric acid solution for quenching, and reacting for 1h under magnetic stirring to obtain a compound 1-1 of the following general formula (1-1):
s1.2, mixing the compound 1-1, catechol, potassium carbonate and N, N-dimethylformamide, heating to 80-100 ℃, adding potassium iodide after 30min, and reacting for 12-24h to obtain a compound 1-2 with a structural formula shown in the following general formula (1-2):
s1.3, mixing anhydrous aluminum chloride and dichloromethane, stirring for 10-30min at the temperature of-20 to-40 ℃, adding a mixed solution of acetyl chloride and dichloromethane and a mixed solution of a compound 1-2 and dichloromethane, and reacting for 4-8h to obtain a compound 1-3 of the following general formula (1-3):
s1.4, mixing the compound 1-3, m-chloroperoxybenzoic acid, trifluoroacetic acid and dichloromethane, placing the mixture in an ice water bath, cooling to 0-10 ℃, stirring for 10-30min, and then placing the mixture in room temperature for reacting for 24-48h to obtain the compound 1-4 of the following general formula (1-4):
s1.5, mixing the compounds 1-4, N-succinimide and trifluoroacetic acid, heating to 50-80 ℃, and reacting for 12-24h to obtain the compound 1 with the following structural formula (1):
4. the method for synthesizing a benzofuran-based luminescent liquid crystal compound according to claim 2, wherein the compound 2 in step S1 is synthesized by:
s1.6, taking a compound 2-1 with a structural formula shown in the following general formula (2-1);
wherein the value range of n is 3-5;
mixing the compound 2-1, p-bromoiodobenzene, anhydrous potassium carbonate, tetrabutylammonium bromide, water, tetrakis (triphenylphosphine) palladium and N, N-dimethylformamide, stirring at 80-100 ℃, and reacting for 8-12h to obtain a compound 2-2 of the following general formula (2-2):
wherein the value range of n is 3-5;
s1.7, mixing a compound 2-2, 2-methyl-3-butyn-2-ol and triethylamine, stirring at 60-80 ℃ for 10-30min, and adding cuprous iodide, triphenylphosphine and tetrakis (triphenylphosphine) palladium to obtain a crude product; adding alkynol, sodium hydroxide, ethylene glycol ethyl ether and toluene into the crude product, heating to 60-80 ℃, and reacting for 6-10h to obtain a compound 2 with a structural formula shown in the following general formula (2):
wherein the value range of n is 3-5.
5. The method for synthesizing a benzofuran-based luminescent liquid crystal compound according to claim 2, wherein in step S2, lithium diisopropylamide and a saturated ammonium chloride solution are both added dropwise through a constant pressure dropping funnel.
6. The method for synthesizing benzofuran-based luminescent liquid crystal compound according to claim 2, wherein in step S1, the molar ratio of compound 1 to compound 2 is 1: 0.5-1.5.
7. The method for synthesizing benzofuran type luminescent liquid crystal compound according to claim 2, wherein in step S2, tetrahydrofuran is used in an amount of 50 to 100mL per gram of compound 3.
8. Use of the benzofuran-based luminescent liquid crystal compound as defined in claim 1 in a liquid crystal display.
9. The use of benzofuran-based luminescent liquid crystal compound according to claim 8, wherein said liquid crystal display is a host-guest mode liquid crystal display.
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